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Methyl iodide → 3-Fluoro-2-methoxybenzaldehyde

HRID 1821668
Notes
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Reaction equation

HRID 1821668 reaction equation
[C:1](#N)C.[F:4][C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9].C(=O)([O-])[O-].[K+].[K+].CI>O>[F:4][C:5]1[C:6]([O:13][CH3:1])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 125722773-Fluoro-2-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To an acetonitrile (50 mL) solution containing 3.01 g (21.5 mmol) of commercially available 3-fluoro-2-hydroxybenzaldehyde were added 5.92 g (42.8 mmol) of potassium carbonate and 6.66 mL (107 mmol) of methyl iodide, and the mixture was stirred at 90° C. for 3 hours. After allowing to stand at room temperature overnight, the reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 3.22 g of a crude product of 3-fluoro-2-methoxybenzaldehyde.

Workup

  1. waitto stand at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-adb3fca026824d1988e823a7c7a68ad2
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608563B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes